12 Radically Honest Questions To Ask Your Dates

It's not rude to be direct.

Rachel Krantz

Sep 19, 2018 | 4:04 AM

I’m a big believer in cutting some of the crap when it comes to how we’re told to behave on dates. It’s mostly being in my first non-monogamous relationship that’s taught me this lesson — anyone I go out with will have a lot of questions about how my relationship and sex life work, and I feel it’s my responsibility to be as open as possible. It took me a couple of years, but I’ve come to realize I deserve the same honesty in return.

We have a misconception in our culture that directness is the same as rudeness, but it’s actually quite the opposite — what’s kind about lying or telling someone a half-truth you think they want to hear? I like to practice radical honesty instead. Delivered and received with kindness rather a judgment, it is actually the much more compassionate way to be, even if certain conversations aren’t always easy to have.

With that in mind, here are some “awkward” or even “rude” questions that most people end up actually appreciating. And if they don’t? Well, that information should save you some time too.

1. What are you looking for right now?

This is one many of us want to ask but don’t because we don’t want to “ruin things.” Take a minute to examine that logic: if you ruin things simply by asking a direct question about something so fundamental, is that relationship really worth your time? Women especially tend to have a fear of being “that girl” asking “that question,” but I find many people are often relieved to be asked this directly.

I preface the question by saying that there is no wrong answer besides a dishonest one and add that my date doesn’t owe me anything except their frankness. I won’t be angry with them, especially early on — I’m just trying to have all the information before I get more invested.

Recently, asking this question helped me avoid sleeping with someone who seemed like a relationship guy but who it turned out only wanted casual sex. Nothing against casual sex, but I’m really glad I found that out before getting disappointed when he failed to live up to expectations I’d based on fantasies.

2. So, who else are you dating right now?

I’m a fan of going for this one on the first date — how much they stumble over being honest reveals a lot about a person. Everyone is dating around, and the earlier you find out how deep in they are with other people, the less you’re going to have to worry that you seem like you’re trying to have “the talk.” You just want to know the situation, and to gauge whether this person is emotionally mature enough to be upfront with you.

Phrasing it this way (assuming they’re dating other people rather than asking if there are) will also help them not feel judged. If the answer is “no one,” they can still say that, but you’re not trying to “catch them” in the act of dating other people.

3. What are your feelings about monogamy/non-monogamy?

This is a question I never asked before I found myself in a non-monogamous relationship, but even if I one day date monogamously again, I’ll continue to ask it. It’s a pretty fundamental thing for two people who are potentially going to knock parts (and/or hearts) to know about each other, even if you’re not on the same page.

4. When were you last tested?

If you don’t want to ask this one over your first drink, I understand. That said, I’ve learned that I almost always end up regretting it if I don’t pose this question until right before I’m about to have sex with someone (or worse, if I don’t ask at all). Not only does their answer tell you their STI status, but how they react to the question will show you if they’re comfortable being an adult about sex, how honest they seem, and to what degree they prioritize safety and health. In my experience, people who say things like, “It’s been a long time, but I always use condoms” or “I don’t have any symptoms, so…” and leave it there? Usually not the most grown-ass of contenders.

If you make having recent test results a prerequisite for sleeping with you, it also gives them a chance to show they’re serious about dating you and helps slow things down by a couple of weeks in a (subversively) old-fashioned way.

5. Why did your last relationship end?

This question gives you a lot of information: how reflective they are, what their relationship history is, where they might currently be at, and how much blame they tend to put on other people rather than themselves. Beware of dates who degrade their ex or use words like “crazy” without reflecting on their own role in the dynamic.

6. Why do you think you’re single?

This is another question that shows how self-reflective someone is and how much they tend to place blame on others. If you’re really feeling them, there’s also a way to ask this question that can come off as quite the compliment. (Avoid the cliche, “So, how is a catch like you single?” but put your own spin on the same sentiment.)

7. So…what was that?

I ask this one if someone does something straight-up obnoxious and rude or otherwise unaware. Calling them on it — again, in a level and kind way — is actually a great way to draw their attention to the fact that they might have offended you. At best, they’ll have a chance to recover, and at the least, maybe they’ll think twice before they do it to the next person.

8. Do you have any deal breakers I should know?

You can also phrase this one as, “how do you feel about [insert your ethical deal breaker here]?” It could be eating animals, having kids, Trump — whatever. Better you find out sooner rather than later.

9. What was your longest relationship like?

Especially if you’re going out with someone in the hopes of a serious relationship, you might as well find out whether they’ve been able to commit in the past. If someone is 45 and has never been in a relationship longer than a year, I’m not saying they should be disqualified — but knowing that (and why) might help temper your expectations. Likewise, if someone just got out of a seven-year marriage, maybe that’s information you’d like to have.

10. So, what do you plan to do about it?

I like to ask this question when someone is talking about how they hate their job or politics or is otherwise being negative. Everyone complains, but whether they can complain and be proactive tells you a lot about someone. This is also a good way to respond when someone is being generally cynical about dating. If they’re worth your time, they’ll be caught off-guard by your calling them on it gently— and then rapidly impressed by you.

11. How am I different than what you thought I’d be like?

This gives you some good information about how your profile is reading, and also lets them a) show you how honest they can be and b) let you know if they’re feeling you. Asked with confidence, it makes you look very secure, which is always sexy.

12. So, what else do you want to know about me?

I used to fill all the silence on dates with questions for the other person — it’s a way we subconsciously ingratiate ourselves. Now, I’ve learned that someone going on a long monologue without giving you a chance to speak in return can be a major red flag. Sure, some people are just chatty, but pay attention (again, perhaps especially if you’re a woman who dates men, because of socialized-gender-bullshit) to whether they ask you any thoughtful questions in return. If you’ve been nodding for five minutes straight, let the next silence hang and then drop this question that brings the focus back to you.

I also think this is a strong way to end a first date, even if they have already asked you plenty — it’s confident, signals your interest, and gives them a chance to ask whatever they may still be wondering (also highly recommend this one for job interviews). And if they can’t think of anything? Well, that’s information you can use, too. Who you are certainly merits further investigation.